Noval benzimidazole and azabenzimiazole derivatives which are thromboxane receptor antagonists, their methods of preparation and pharmaceutical compositions in which they are present

US5021443A · kind A · utility

Assignee

• Laboratories UPSA · FR

Inventors

• Nicole Bru-Magniez · Paris, FR
• Eric Nicolai · Paris, FR
• Jean-Marie Teulon · La Celle-Saint-Cloud, FR

Key dates

• Filing date: Mar 15, 1990
• Grant date: Jun 4, 1991
• Expiry date: Mar 15, 2010

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07F9/6561
• WIPO field: Pharmaceuticals
• WIPO sector: Chemistry

Abstract

The present invention relates to the derivatives of the formula ##STR1## in which: A is an aromatic ring or a nitrogen heterocycle; PA0 X.sub.1, X.sub.2, X.sub.3 and X.sub.4 are independently a hydrogen atom, a halogen atom, a lower alkyl radical, an alkoxy radical, an alkylthio radical, a sulfone group, a sulfoxide group, a trifluoromethyl group, a nitro group, a hydroxyl group, a methylene alcohol radical or a group COOR', in which R' is a hydrogen or a lower alkyl; X.sub.3 and X.sub.4 can also form a naphthalene with the phenyl; PA0 B is CR.sub.5 R.sub.6, R.sub.5 and R.sub.6 being a hydrogen atom or a lower alkyl, or the sulfur atom; PA0 R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are independently a hydrogen atom or a lower alkyl radical; CR.sub.1 R.sub.2 or CR.sub.3 R.sub.4 can form with B, when the latter is CR.sub.5 R.sub.6, a cycloalkyl or a cycloalkene having 3 to 7 carbon atoms; R.sub.1 R.sub.2 and R.sub.3 R.sub.4 can also form a ring having 3 to 6 carbon atoms; PA0 n is an integer from 1 to 4 and can be 0 if R.sub.1 and R.sub.2 are other than hydrogen; and PA0 D is a chemical group which can be: COOR.sub.7, R.sub.7 being the hydrogen atom or a lower alkyl, CONH--R.sub.8, R.sub…